Rosie O’Donnell’s Kimmel Week: Here’s What We Know So Far

When Jimmy Kimmel announced the guest hosts for his annual two-month summer break, he saved the most loaded booking for last: Rosie O’Donnell—Donald Trump’s longest-running celebrity antagonist. Kimmel framed her week behind the desk as a parting gift to the president. Two months later, it’s shaping up to be the most anticipated guest-host stint in recent late-night memory.

O’Donnell has spent the run-up talking about the assignment—on social media, on Late Night with Seth Meyers, and most recently in a sit-down with Kara Swisher—laying out what she wants to do behind the desk and what ABC has already told her she can’t.

Here’s what we know.

When Is Rosie O’Donnell Hosting Jimmy Kimmel Live!?

O’Donnell is scheduled to host Jimmy Kimmel Live! the week of August 17—a full four nights in the chair. Her visit will mark the penultimate week of Kimmel’s summer guest-host rotation, which has already handed the desk to Tiffany Haddish, Ike Barinholtz, Colman Domingo, and Anthony Anderson. Musician Jelly Roll will pick up the baton from O’Donnell starting August 21. (Kimmel is set to return the day after Labor Day.)

How Did the Booking Come About?

Kimmel announced his summer host lineup on his June 18 broadcast and made clear he knew exactly what kind of booking he was making. Saying he’d be off for two months “this time voluntarily”—a wink at his suspension last fall—he called O’Donnell “one of [Trump’s] all-time favorites” and “a special treat for our commander in chief,” brought in to “keep the hits coming.”

Has She Ever Been on the Show Before?

No—not even as a guest. O’Donnell’s guest-host week will be her first-ever appearance on Jimmy Kimmel Live! in any form. “I’ve never been on his show, so this will be the first time as the guest host,” she told Swisher, adding that she’s “thrilled” Kimmel gave her the full week.

What Does She Plan to Do About Trump?

Her stated approach is to do what Kimmel does. Previewing the week on Late Night with Seth Meyers, she said she intends “to be a good soldier for [Kimmel] and do what he’s been doing so well for a week so he can have a nice vacation.”

She’ll come at Trump “in a comedic, honest, truthful way,” she told Swisher, working with the show’s writers and staff and “honoring just how brave and bold [Kimmel] has been.” Despite Disney’s current friction with the FCC, she waved off the prospect of any agency blowback—”What are they going to say, that you can’t say that?”—and floated opening her first night with a mock love song imagining the president as her secret admirer.

She won’t have a completely free hand, though. ABC has already told O’Donnell it can’t clear a Trump song parody that appears in her stage show—set to the tune of “If I Only Had a Brain”—citing licensing issues caused by the “political content” of her rewrite.

Who Are Her Guests?

O’Donnell’s four-night lineup is now set: Hannah Waddingham and Ana Gasteyer on Monday; Jean Smart and Richard Gadd on Tuesday; Charlie Day and Janelle James on Wednesday; and Nick Offerman and Megan Mullally, Shawn Hatosy, and Sydney James Harcourt on Thursday.

It’s an especially Emmy-heavy group. Five of O’Donnell’s guests—Smart, Gadd, James, Offerman, and Hatosy—are nominees at next month’s Emmy Awards. That’s no coincidence: final-round Emmy voting begins Monday, August 17, the same day O’Donnell starts her week behind Kimmel’s desk.

There are some O’Donnell connections in the mix, too. She’s longtime friends with Mullally, appeared in the fourth season of Hacks, which stars Smart, and has previously singled out Harcourt’s stage work for praise.

One guest O’Donnell had hoped to book didn’t make the cut: children’s educator Ms. Rachel, whom she likened to “Mr. Rogers now for our contemporary time” and had hoped to bring on for a doll giveaway. “She couldn’t make it or they couldn’t book it,” O’Donnell told Swisher.

Is She Angling for a Full-Time Return to TV?

Not to late night. After a Globe report claimed she was plotting to take over Kimmel’s show for good, O’Donnell posted her reply to the reporter on Instagram: “Ha funny—and completely untrue.” She’s not interested in late night, she wrote—but added that daytime “would be interesting.”

That daytime itch is apparently real, and she’s gotten specific about it since. In an episode of Kyle Ridley’s The Tangle podcast this week, O’Donnell said a new show “would look a lot like my old show,” leaning on nostalgia and human interest over celebrity promotion—”I think celebrity culture is dead in America.”

She talked about telling good news, booking Broadway, and playing “fun and games with people like we used to,” with any star visits there to hang out rather than plug a project. She’d weigh a streaming home, calling the syndication market “pretty much dead,” and said her agents are “taking meetings.” The one condition: she wants it to launch only “when Trump is no longer in power.”

Daytime talk has thinned sharply in recent months, with The Kelly Clarkson Show, Sherri, Karamo, and The Steve Wilkos Show all ending their runs—an opening O’Donnell seems eager to fill on her own terms.

What’s Next for Her After the Week?

Not much of a victory lap. O’Donnell is currently in New York for a short run of her one-woman show Common Knowledge—about her relocation to Ireland, her family, and Trump—and is scheduled to head back to her adopted home of Dublin after the Kimmel week, where her youngest is in school. She’s described her return to the States this summer, guest-hosting included, as leaving her feeling “refamous.”

Why It Matters

O’Donnell isn’t like the rest of Kimmel’s summer bench; she’s a political lightning rod who’s been feuding with Trump for two decades. Booking her to “keep the hits coming” reads less as a vacation stopgap than as Kimmel extending his own antagonism of the president by proxy—keeping the pressure on for a week even while he’s off the air.

It also all but guarantees the president will be watching. Trump has never been able to tune O’Donnell out, and a week of her at Kimmel’s desk is tailor-made for his attention; whether he chooses to broadcast a reaction is the only real question.

For its part, ABC has shown more spine than most. Since his September suspension—reversed within days after a backlash that knocked billions off Disney’s market value—the network has stood behind Kimmel, signing him to an extension through May 2027, and citing him in reaction to the FCC’s early review of its station licenses, which it has flatly called political “retaliation.”